Regioselective epimerisation of cis-3-Amino-4-oxo-azetidine-2-sulphonic acid and synthesis of monocyclic β-lactams (CROSBI ID 86335)
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Podaci o odgovornosti
Cerić, Helena ; Kovačević, Miće ; Šindler-Kulyk, Marija
engleski
Regioselective epimerisation of cis-3-Amino-4-oxo-azetidine-2-sulphonic acid and synthesis of monocyclic β-lactams
A novel procedure for the regioselective epimerisation of cis-3-amino-4-oxo-azetidine-2-sulphonic acid (3-AAA)into the trans-isomer is described. It was found that a compolete inversion of C-3 configuration of the cis-3-AAA takes place during the formation of a Schiff base. The cleavage of the imine bond of the Schiff base in methanol resulted in the generation of trans-3-AAA in good yield. Here is also described a preparation of novel cis- and trans-monobactams with an amidosulphonic acid group on azetidinone nitrogen.
azetidinones ; epimerisation ; imines ; sydnones
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